George’s Chin
How a simple mistake in second grade taught me everything about imperfection, courage, and showing up.
In second grade, we were asked to draw the picture above the classroom blackboard — a portrait of George Washington. I remember making a mistake on George’s chin and feeling sad about it. But when I brought the picture home, my mom and dad thought it was “the best thing in the whole wide world.” They even framed it. That drawing hung in my childhood home for nearly 60 years, and now it’s on my office wall, looking over my right shoulder, visible to anyone on Zoom with me. It’s a daily reminder that it’s always okay to make mistakes — and that you can still be loved and celebrated.
Putting myself out there was second nature. Messy work was what I turned in, never obsessing about typos and spelling like some of my friends did. I paid with red marks, do-overs, and sometimes lower grades. But it didn’t make me neater or more detail-oriented. Instead, it made me bolder and riskier in how I expressed myself — whether writing, speaking, or sharing ideas.
Most teachers were rigid—more focused on making us spit out our gum or fix our skirts than encouraging creativity. But a few, like my Spanish teacher who let us make Mexican food and bring it into class for a fiesta with dancing, coaxed the creative spirit out of me. I wanted to please them.
Over 20 years ago, when I started my first business, I discovered I was a writer. The freedom I felt when I put my thoughts on paper was exhilarating. Hours would melt away as I lost myself in writing. Subscribers often replied, moved by what I’d written. They didn’t know I often wrote these emails at 6am, first cup of coffee in hand, pressing send before I was fully awake. Stories were shared honestly and vulnerably.
That early experience of honest expression naturally led me to mentoring others in their own journeys. Over the past twenty years, I’ve helped hundreds and hundreds of clients break free from perfectionism disguised as procrastination. I’ve held their hand as they pressed send on their laptops and coached them to accept that their writing will never be “done”—rather, it’s “done enough.”
Perfection can feel like a safe place to wait—but it’s also a place that holds us back. That old drawing reminds me it’s okay to mess up and still be enough. Maybe that’s a good place to start.
What’s one imperfect moment that helped shape you? That kindness, together with the love of George and my parents, has shaped who I am today.